Literature DB >> 18461954

Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.

Dmitri Chernyak1, Surendra Babu Gadamsetty, Vladimir Gevorgyan.   

Abstract

Organocopper reagents smoothly react with heterocyclic propargyl mesylates at low temperature to produce N-fused heterocycles. The copper reagent plays a "double duty" in this novel cascade transformation, which proceeds via an SN2' substitution followed by a subsequent cycloisomerization step.

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Year:  2008        PMID： 18461954      PMCID： PMC2615671          DOI： 10.1021/ol8008705

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  32 in total

1.  Wherefore Art Thou Copper? Structures and Reaction Mechanisms of Organocuprate Clusters in Organic Chemistry.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-03       Impact factor: 15.336

Review 2.  Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

3.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

4.  Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors:  Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

5.  Selective partial reduction of various heteroaromatic compounds with bridgehead nitrogen via Birch reduction protocol.

Authors:  Joseph T Kim; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

6.  A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors:  A V Kel'in; A W Sromek; V Gevorgyan
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

7.  Electrophilic fluorodesilylation of allenylmethylsilanes: a novel entry to 2-fluoro-1,3-dienes.

Authors:  Ma Carmen Pacheco; Véronique Gouverneur
Journal:  Org Lett       Date:  2005-03-31       Impact factor: 6.005

8.  Pharmacokinetics and pharmacodynamics of TF-505, a novel nonsteroidal 5alpha-reductase inhibitor, in normal subjects treated with single or multiple doses.

Authors:  Tomoe Fujita; Yoshiaki Matsumoto; Toshimi Kimura; Shinichi Yokota; Mika Sawada; Masataka Majima; Yoshio Ohtani; Yuji Kumagai
Journal:  Br J Clin Pharmacol       Date:  2002-09       Impact factor: 4.335

9.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

10.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419
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  9 in total

1.  ORGANOCOPPER-MEDIATED TWO-COMPONENT SN2'-SUBSTITUTION CASCADE TOWARDS N-FUSED HETEROCYCLES.

Authors:  D Chernyak; V Gevorgyan
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-03-01       Impact factor: 1.277

2.  Palladium-catalyzed intramolecular carbopalladation/cyclization cascade: access to polycyclic N-fused heterocycles.

Authors:  Dmitri Chernyak; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-11-08       Impact factor: 6.005

3.  Two-component approach toward a fully substituted N-fused pyrrole ring.

Authors:  Dmitri Chernyak; Cathy Skontos; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

4.  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors:  Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2015-12-01       Impact factor: 6.005

5.  On the validity of Au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Yahong Li; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2010-11-11       Impact factor: 6.005

6.  Synthesis of a novel chemotype via sequential metal-catalyzed cycloisomerizations.

Authors:  Bo Leng; Stephanie Chichetti; Shun Su; Aaron B Beeler; John A Porco
Journal:  Beilstein J Org Chem       Date:  2012-08-20       Impact factor: 2.883

7.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825

8.  Metal free C-3 chalcogenation (sulfenylation and selenylation) of 4H-pyrido[1,2-a]pyrimidin-4-ones.

Authors:  Prasanjit Ghosh; Gautam Chhetri; Sajal Das
Journal:  RSC Adv       Date:  2021-03-09       Impact factor: 3.361

9.  A simple and efficient copper-catalyzed three-component reaction to synthesize (Z)-1,2-dihydro-2-iminoquinolines.

Authors:  Xiai Luo; Yu Zhao; Susu Tao; Zhong-Tao Yang; Hui Luo; Weiguang Yang
Journal:  RSC Adv       Date:  2021-09-29       Impact factor: 4.036
  9 in total

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